


A Pretty Damn Big Win

by supernaturalbook



Category: Supernatural
Genre: Alternate Season/Series 12, Caring Dean Winchester, Crying Dean Winchester, Cute Dean Winchester, Dean Winchester Actually Deals With Feelings, Dean Winchester Feels, Dean Winchester Flirts With Reader, Dean Winchester Loves Reader, Dean Winchester Loves The Impala, Dean Winchester Needs a Hug, Dean Winchester Needs to Use Actual Words, Dean Winchester is Loved, Diners, Established Relationship, F/M, Fluff, Gentle Sex, Lovesick Dean Winchester, Loving Dean Winchester, Protective Dean Winchester, Reader Drives The Impala, Reader Loves Dean Winchester, Reader-Insert, Road Trips, Romantic Fluff, Semi-Public Sex, Sex in/on the Impala (Supernatural), Sleeping in the Impala (Supernatural), Slow Dancing, Stargazing, Stress Relief, Surprises
Language: English
Status: In-Progress
Published: 2019-08-16
Updated: 2019-08-16
Packaged: 2020-07-26 18:10:12
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,471
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/20031172
Author URL: https://archiveofourown.org/users/supernaturalbook/pseuds/supernaturalbook
Summary: Things are getting pretty stressful in the Winchester's lives. No, there's no looming apocalypse this time, but things still seem to be falling apart more and more every day. And to make matters worse, there's nothing you can do about it yet, and the stress is taking a toll on all of you. In the middle of all of this, Dean Winchester proposes that the two of you go on a road trip together, just to get away from it all. After all, spending time with his loving girlfriend was just what he needed-A win.





	A Pretty Damn Big Win

_Ugggh_. 

It was way too early to be awake but, truth be told, he never got to sleep in the first place. Dean Winchester rubbed his hands over his scruffy face and sat up in bed before deciding to just sit and watch his girlfriend for a moment. He would inevitably have to drag his ass out of bed, but for now, he wants to take the time to appreciate your presence. _God, look at you, baby. _You looked so calm, so small and helpless lying next to the disgruntled hunter, the lumbering oaf that was Dean Winchester. Sometime during the night, you had curled yourself around him in an intimate embrace, one that Dean hadn’t been used to before knowing you. 

Dean Winchester was a good man, but he did have his faults. For instance, his post-hunt ritual wasn’t always to shower and snuggle up in bed with his one true love. Rather, he’d drive himself to a bar to get tipsy and find any woman who he wanted to lose himself in that night, only to leave as soon as he could in the morning. Sure, he’d have someone to hold on those nights, but laying with a stranger after sex could never compare to the embrace of two lovers who shared each other’s hearts and souls. He knew that now, and he found himself wondering- once again- what he did to deserve someone like you. Someone who’s such a contrast to his cold, dark life. 

He knew from the moment he met you that you were going to be the death of him, and he was ready to accept that fate happily. When he was younger, he had flirted innocently with you every now and then, just watching to get a reaction out of you, wondering if you would ever be his. You made him _feel _things. Good things- hell, _great _things. Things he hadn’t felt in such a long time. 

God, that was so long ago. How did it take him so many years to get a hold of you? ‘_Not my fault’,_ Dean mused, ‘_she makes me feel like an awkward kid again. She makes me all flustered and shy when she smiles. And her laughter, God, it’s so beautiful. And the way she says my name…’ _His face was flushing just at the thought.

In your sleep, you snuggled closer into Dean’s side and used your leg- which was tossed over his own- to try and pull him closer to you. 

“Sorry, sweetheart. Gotta get up now.” He pressed a kiss against your forehead and when you _still_ didn’t stir from your slumber, he realized just how tired you must have been. Recently- he’d be completely honest- things haven’t been going so well in the Winchester’s life. Things weren’t quite as bad as they’d been in the past- there was no looming apocalypse, thank God- but the stress of all the hunts was still taking its toll on all of you. Especially you, _bless your precious heart._ Who knows what you were trying to do, staying up late to research and wearing yourself out like that for him and Sammy. Dean would never, _ever_ be able to find the right words to thank you for all you’ve sacrificed for them. The most stressful thing about all of this was that there was nothing you could do yet. Read through all of the books in the library, sure, but you had absolutely no leads and therefore no place to start. And among the stress of trying to figure out what to do, there seemed to be so many cases. Much more than usual. “God, I’m sorry (Y/N). You deserve so much more than this life.” He decided to let you sleep in a while longer and grudgingly pulled himself out of bed, groaning when his feet hit the cold floor. He turned back momentarily- he could never really get enough the girl who gave up _everything_ for him and gave _him_ everything, could he?- and tucked the blankets warm and snug around your form, smiling to himself.

‘_Oh baby, you’ve got me wrapped around your finger, you know that? And I wouldn’t have it any other way.’_

Okay, something was off. 

It was early morning when you woke up to the sound of your lover’s heavy, booted feet moving around on the hard floors of your shared bedroom. You cracked your eyes open and looked around for any indication of what time it was. There were no windows in the bunker, but your eyes fell on the digital clock on the nightstand. _Three in the morning? What’s Dean doing up at 3 am? _You drearily noticed that Dean had his and your duffel bags on the edge of the bed, each half-filled already.

“Dean?" You shuffled around on the bed, indicating to him that you were awake. In your half-asleep state, you immediately jumped to the worst conclusion. _Oh God, something bad happened and now we have to get out of the bunker before we die._ "What’s happening? Where are you going?” Dean looked up at the sound of your voice, a genuine smile taking over his face at the sight of you in his bed. It wasn’t odd for you to sleep in his bedroom- you’d been dating for two years now- but you could always see how thrilled Dean was to see you there every morning. 

And God, it had been way too long since you saw him smile at you like that, despite the eyebags.

Dean had a habit- maybe not a habit, a _curse_\- of staying up too late for his own good and not getting any sleep some nights. Not his fault, and you couldn’t blame him- hell, if you had _half_ the emotional and psychological trauma he did you wouldn’t be able to sleep either. Most of the time it was nightmares -his time in hell, in purgatory, a particularly bad hunt- and sometimes just plain old memories. He was often haunted by memories of the past, guilt over things long gone, the deaths of people who he could never save and still blamed himself for, and the worry- scratch that, the fear- of losing you. You would always be able to tell when he had a night like that. Aside from the telltale eyebags and many, _many_ cups of coffee, he’d carry himself less proudly, be less talkative- it was always worrying when he didn’t crack jokes with you- and overall be the spitting image of a _broken man._

Something was different today- _ahh_, this _morning_, at 3 am. He was… _excited_.

“Morning, sleepyhead.” He leaned down to lay a kiss on your forehead, dragging his hand over your messy hair. “I was just about to wake you up.” His gentle gesture and happy demeanor calmed your worried mind. Nothing bad was happening; he doesn’t seem worried or rushed. In fact, he seemed… _softer,_ calmer than usual. You sat up in bed, watching him lay items out on the bed to pack. 

“So… what’s going on?” You rubbed the sleep out of your eyes.

“You and I are going on a road trip for the weekend. Or however long we can be away." 

"Without Sam?" 

“Well, it wouldn’t be much of a romantic getaway if I brought my little brother with, would it?” He caught your confused gaze and laughed. "What, I can’t go on dates with my girlfriend?”

“That’s not what I meant. Is there, like, a hunt or something?” Dean opened your dresser and tossed you a pair of your jeans and one of his big Led Zeppelin tees. 

“No. No hunts this week. Told Sammy we all need a break. Gotta get out of here, don’t you think? I’m suffocating” He turned to you again, leaning in to give you a squeeze and help you out of bed. “Anyway, we need to go on a date again, ya know? It’s been a while. Come on, get up, sweetheart. I’ll keep packing, you go get dressed. We’re wasting driving time.“ You happily jumped out of bed to get ready, taken aback by how sweet Dean was acting, considering how stressed he had been the day before. Not even 24 hours ago, Dean was downing a bottle of whiskey and stressing over everything that had been happening recently. “_I just need one win. Just one._” he had muttered into his glass before downing it and letting the familiar drink burn down his throat. It was odd that he suddenly seemed cheerful and happy again, but you’ll be damned if you’re not gonna cherish _every single _moment of Dean’s sweet side. ‘_God_,’ you thought, thinking back to your past with him. ‘_His sweet side is what made me fall for him in the first place’. _

When you first met Dean, you knew _immediately_ that you’d fall in love with him. 

You were born into a family of hunters, who eventually- of course- met a tragic fate like many others, while you managed to get out of the life and were in the midst of your college education. Two FBI agents- odd, it didn’t really require the FBI- came to your dorm to ask you about it. 

They were both tall and imposing, one a bit taller than the other, and they were both quite handsome, you’d admit, but your eyes lingered on the shorter of the two. He had short dirty blonde hair and, once they sat down across from you and you could see him closer, you noticed the freckles sprinkled across his face. And the way the light hit his cheekbones- _God he was pretty._ You had to stop yourself from staring at his eyes- _they were so beautifully green-_ while he questioned you.

And boy, this man sure didn’t seem to care if there was a difference between questioning and _flirting_. Because you got a decent amount of both, leaving you flustered and _fucking aching _for him before you even knew his name.

They asked strange questions, but questions that struck a familiar chord in you. “Did you smell anything strange when you found them?” You knew why they were asking, and it reminded you of the information your parents told you to keep you safe. _Sulfur equals demons. _Were these guys hunters too? So, in the midst of their interrogation, you broke out your own questions. “_Do you believe in demons?”_ They froze- surprised when they learned you came from a hunting family and asked for your help on the hunt. They introduced themselves- Sam and Dean Winchester. “_The_ Winchesters?” Your parents told you about John Winchester- their father- and here you were, meeting his sons. 

Well, their parents sure make pretty babies.

After you helped them on the hunt, you knew there was no way you could continue living normally, but Sam and Dean helped. They introduced you to a friend of theirs- Bobby Singer- and persuaded you to stay with them to ensure your safety. Sam told you later that Dean was the one who suggested having you stay at Bobby’s and who wanted to keep in touch with you.

You stood in the doorway of the bathroom, brushing your teeth and watching Dean dig through your dresser and looking up every now and then to have you confirm the outfits he chose. You answered in small sentences, still lost in memories of when you first met. 

You weren’t going to lie- the first things you noticed about Dean was how handsome he was. Not only in appearance, even though he was goddamn pretty- but in the way he _held_ himself. He was confident, but not egotistical- just enough to be attractive and flirtatious without the whole douchebag vibe. He knew how to make you (and basically every hetero girl he ever interacted with) flustered with just a look and _damn_, he knew he was good at it. You eventually learned he wasn’t just a pretty face. He had the best sense of humor- some of the funniest lines you’d ever heard belonged to him- and was always super selfless, even to the point of self-sacrifice. And, when he wanted to be, he was sweet. He went out of his way to keep you safe and comfortable, no matter the situation. Need a bodyguard while in a bar? _‘Got__ you, __sweetheart’. _You’re scared about walking into this next hunt? _'Just__ stay behind me. Nothin’ will hurt you long as I’m here’. _You just plain need a hug? _'Aw. C'mere, kid’._

You could still remember the conversation you had with Dean before they left you with Bobby after that first hunt together. “Remember, you’re only staying here so you don’t get hurt. Don’t just throw your life away for hunting, kiddo.” 

“I’m not a kid, Dean. I’m twenty-two. I’m only six years younger than you.” He gave you a stern look. 

“Don’t change the subject, (Y/N).” You sighed, but couldn’t help but smile. _He cares about you. He doesn’t want you to get hurt._

“Alright. I won’t go looking for hunts, but If you’re in trouble, I’m not just gonna sit by and watch. I’m gonna help.” After they had loaded their stuff into the Impala and were ready to drive off, Dean looked at you again, making you promise to stay safe. “Only if you do too.” You could still remember- _vividly_\- how Dean gave you a quick wink and a smirk right before they drove off. 

Little did they know, that was the beginning of your long friendship with them.

Smiling at the fond memories of him, you left your spot in the doorway to wrap your arms around Dean’s waist from behind, earning a soft grunt from him. “Well, hey there.” He turned around in your arms and kissed the top of your head, taking a moment to breathe in your scent. 

“I love you, Dee.”

“Love you too, sweetheart.” You continued to pack your stuff up and get ready, seeing that Dean had already laid out most of your toiletries and your favorite outfits- consisting of mostly Dean’s shirts. When you finish, you grabbed a big, warm flannel out of Dean’s duffel bag and pulled it on, surrounding yourself with Dean’s scent and warmth. He gazed at you with an attentive grin; he always loved when you wore his clothes. After shrugging on his jacket and grabbing his duffel bag, Dean turned to you and looked you over one last time, a big, toothy grin taking its place on his face. “You ready?” 

“One hundred percent.” you grabbed one of his hands in yours as you made your way out to the garage, where your black beauty awaits you. Dean smirked and twirled the keys to the Impala around his finger.

“Then let’s get out of here, baby.” 


End file.
